


Prison Bitch

by curtainsup



Category: Original Work
Genre: Abuse, Anal, Anal Fingering, Anal Fisting, Anal Play, Anal Sex, BDSM, Blow Jobs, CBT, Cock & Ball Torture, Cock Worship, Dom/sub, Enemas, Exhibitionism, Fisting, Forced Orgasm, Guards, Humiliation, Inflation, M/M, Master/Slave, Multi, Oral Sex, Orgasm Control, Orgasm Delay/Denial, Prison, Public Blow Jobs, Rape, Rape/Non-con Elements, S&M, Verbal Humiliation, Violence, Voyeurism
Language: English
Status: In-Progress
Published: 2015-11-28
Updated: 2016-01-09
Packaged: 2018-05-03 19:47:32
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 4
Words: 10,485
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5304491
Author URL: https://archiveofourown.org/users/curtainsup/pseuds/curtainsup
Summary: <blockquote class="userstuff">
              <p>Kyle meets his new prison bitch - a cute college kid with a pretty mouth and a tight, virgin ass. James' life will change forever, and every secret fantasy he has will be explored (and more), whether he wants it or not.</p>
            </blockquote>





	1. Introductions

James had never had to share a room with another man in his life. He'd never had a brother, he'd lucked out for his first year of college and snagged a single room, and then his whole life had changed. The guards escorted him down the halls, the sound of men stomping their boots and smacking their cell bars following him. James hung his head, his blond hair falling into his face. He was - or had once been - a cute college kid. He was a little nervous, a little bookish, his frame slender and light. With his big blue eyes, his full cocksucking lips and the cute glasses perched on his nose, he looked like the prison would eat him alive.

It had been a stupid mistake. Just once, he'd wanted to fit in. He'd had a few too many, and when his 'friends' had run out of beer, they had sent him out to get more. He knew that it was stupid, but he had been feeling flushed and flattered by all the attention. He hadn't wanted the guys to leave. So he'd gotten in his car, and he'd gone to buy beer. It was only three blocks away, what could possibly go wrong?

He ran over a little girl a block away from home, beer in the back seat. Child killer. Men (though at nineteen, he was little more than a boy) like him didn't get it easy in prison. The guards shoved him into his cell, un-cuffed him and shut the bars behind him, leaving him to his fate.

"Enjoy, princess," one said as they walked away laughing - Steve had lost his wife to a drunk driver years earlier, and he didn't take kindly to those that killed others through sheer stupidity. The guards could have been easy on the boy, could have put him with someone that wouldn't make his life a living hell, that would shelter him without taking it out of his ass, but they wanted to see James suffer. He was a pretty boy - by the end of the week, he'd have bent over for half the prison. And they had made sure to bunk him up with one of the guys with the biggest cocks to 'break him in'. Not that James knew his fate yet. He had an inkling from the TV, from rumours and jest, but surely prison couldn't be all that bad? Ever the optimist, James didn't want to think about what could be in store for him.

Kyle was sat up on the top bunk, his muscular back pressed against the wall as he watched his new cellmate, his expression blank. He eyed the boy up, taking in his smooth, pale skin, his lean body and his pretty face. The kid looked barely legal, and that was how Kyle liked them. He felt a tingling in his dick just looking at that innocent face, those big, cute eyes and those full lips. Kyle was betting that those lips had never been wrapped around a cock, though the kid looked like he sucked it constantly. No matter, Kyle would make sure to put those lips to good use. That ass, too.

"Turn around," he said, his voice deep, masculine and authoritative. Kyle was a big guy. At 6'4, he was about nine or ten inches taller than Kyle, and the muscles in his legs were about the size of Kyle's head. His arms were huge and covered in prison tattoos. The bulge in his crotch was pronounced, snaking down one leg. He wasn't even hard yet. He had a buzz cut, his hair dark and cropped close to his skull. His legs hung off the end of the bed.

"W-what?" James stammered, his voice meek compared to Kyle's. There was no doubt that his new cellmate was an alpha male, and James felt like a bug in his presence, like he wasn't a real man. Fuck, the guy bled testosterone. Next to Kyle, James was nothing.

"Turn around," Kyle insisted. "I want to check out that ass of yours." He grinned, his dimples showing, deceptively friendly.

"N-no," James said, his eyes widening. His hands fluttered awkwardly as if he didn't know quite what to do with himself.

"Tch. Boy, you don't want to make me come down there." Kyle's grin shifted, something dangerous lurking behind his eyes. His smile sharpened, showing one too many teeth. "Guards put you in here for a reason. You start screaming, they won't come. Now turn around and show me your ass."

"You can't do this," James said, his eyes filling with tears. He tried to hold them back - he was a man, after all. Men didn't cry. A wave of hopelessness went through him. His life was ruined. Just weeks ago, he had been a happy, carefree college kid. Now he was sharing a cell with a criminal and his life was ruined. He wouldn't be able to go back to college, get a job, anything. That was even if he ever got out of this place.

"I can do whatever the fuck I want," Kyle said, shifting on the bed. He reached a hand down between his legs and squeezed at the bulge in his orange jumpsuit, eyeing the pretty college boy. He liked it when they cried a little - it was real cute. "You wanna know why I'm in here, kid? I'm in here for raping a pretty boy like you. So think about how much you wanna push me. Like I said, they put you in here for a reason. They wanna see you suffer, boy. So turn the fuck around."

At the word 'raping', James' future flashed before him. He had no illusions - this man could overpower him easily. Letting out a helpless sob, he turned around and gripped the bars, turning his back to the other man.

"That's it," Kyle said. "Now stick your ass out real pretty, show me what you're working with, kid. If you've got a nice enough ass, maybe I'll keep you around a while."

James took a deep breath, fighting his humiliation. His cheeks flushed red and he curved his back, shoving his ass out at Kyle. Across the hall, there was another cell, two men watching and nudging each other. James avoided their eyes.

"That's a real nice ass, kid. But I can't see it so well with that baggy as shit jumpsuit on. Why don't you take it off, eh?"

"I don't want to," James said, still sticking his ass out at the man. Tears welled up in his eyes. "Please. Don't make me."

Kyle rolled his eyes - the fucking fag was so pathetic. "Come on, you got underwear under them, not like it's so bad. Strip 'em off for me, or do I have to come down and make you do it? If I have to make you, you better believe I'll be fucking you right up against the bars where everyone can see."

Trembling, James peeled himself away from the bars. His hands shook as he lowered the zip on his overalls. He pulled them from his body and stepped out of them, revealing a white undershirt and a pair of white boxers.

"Tch, kind of skinny," Kyle said. "Ah well, we'll beef you up, get some muscle on you. Even if we can't do anything about the size of your cock. Not that you'll need it that much. Your bulge is real small there, though. How you expect to fuck bitches with that cock? Prolly a good thing you're a faggot."

"I-I'm not. I'm not a fag," James said, his cheeks flushed. He clasped his hands in front of his groin, looking down at the floor and chewing on his lower lip cutely. "My dicks' just average, that's all."

"Average." Kyle snorted. "Sure." He checked the kid out quickly. "Now turn around and lower your boxers down under your ass and show me that sweet ass of yours. If you tell me no again, I'm gonna get off this bed and give you a lesson in obedience, boy." 

Trembling, James turned around again. He took a deep breath, fiddling with the waistband of his boxers. "I can't," he sobbed, even as he lowered them over his ass, showing nice, full, pale buttocks. He stuck his ass out toward Kyle and gripped the bars again, his face flushed.

"That's it," Kyle encouraged. "Yeah, that's real nice, bet that's as smooth as a girl's, huh? Now reach back and show me your pretty pink asshole. I wanna see your cunt, boy."

James whimpered quietly. He hesitated for a long moment, until he heard Kyle move on the bed. James' hands flew from the bars. He parted his own buttocks slowly, revealing his tight, pink asshole. It was obvious just looking at it that he'd never had anything bigger than an exploratory finger up there, despite any curiosity he may have had.

"That's a really cute pussy, James," Kyle said, rubbing his hand over the slowly growing bulge at his crotch. There was a damp spot near the head where he was starting to leak pre-cum. "I'm gonna enjoy shoving my big dick in that. Aren't you glad you saved it for me? Open it up wider so I can see it."

James sobbed brokenly and did as he was told - it had only taken ten minutes to turn him from a once-normal college boy to a crying, broken, obedient thing. He opened his ass up further for Kyle, showing him his tight, puckered hole, ignoring the leering men opposite their cell.

"Have you ever sucked dick, kid?" Kyle said, unzipping his jumpsuit and pulling his cock and balls out. He stroked himself a few times, rubbing his fingers over the sticky, uncut tip.

"N-no," James stammered.

"D'you want to learn? Before you answer, I want you to know that my dick is going in you one way or the other. I can either shove it up your pretty pink asshole, or you can have a little lesson in how to suck cock. I don't care either way. But if you even try to bite, I'm gonna give you a lesson in what it feels like to have your balls tortured whilst a big, thick cock fucks you up the ass. You got it?"

James broke down. He let go of his ass and grabbed the bars again, crying openly. His knees felt weak. The reality of the situation hit him - he was going to be this man's prison bitch. He was going to be little more than a prisoner's sex slave until he either got out of prison or he died.

"I haven't got time for this shit, faggot. You can get over here and start licking my dick, or you can keep crying like a stupid girl whilst I ruin your asshole. It's up to you. I don't really give a shit as long as my thick cock gets a warm hole to fuck, you got me?"

James let out another heart wrenching sob, but Kyle was absolutely unmoved - he wanted to get his dick sucked, and he wanted it now. If James was incapable of sucking his dick, then he'd just shove it up the boy's ass and be done with it. He just liked to lube up with a little throat fucking first. After all, in prison, it wasn't like there was any lube. If the boy sucked him off a little first, it wouldn't hurt so bad when he rammed his thick cock up his ass. If he didn't suck it, it was no skin off Kyle's nose.

Giving in, James straightened up. He pulled his boxers back up over his ass, ignoring the hoots and laughter from those that could see what was happening. They all knew what was coming. Turning around, he looked at Kyle. James was blushing deeply, his eyes bright with tears, his lips quivering. Kyle couldn't wait to get those lips around his cock.

"Come on over," Kyle said, hopping off the bed and leaning against the wall, staying by the cell entrance so he could give his buddies a show. After all, it wasn't like they got fresh meat this pretty that often. "Kneel down. Don't make me make you, bitch."

Trembling all over, James did as he was told. He got down on his knees. The cement floor was cold and crushed the delicate skin at his kneecaps. For the first (though far from the last) time, he came face-to-face with the cock that he was destined to serve. It was a monster - nearly ten inches long and nearly as thick around as a can of coke. Just looking at it made James' stomach cramp and his asshole tighten as he tried to imagine that up inside him.

"There's a good bitch," Kyle said, slapping the head of his dick back and forth over James' face. He pulled the foreskin back and rubbed the head of his cock over the boy's lips, pre-cum clinging between his dick and James' mouth in strands. Kyle lifted his dick up. "Now suck my balls," he said. "Every good dick suck should start with the balls. Bitches forget balls too often."

James leaned in, trying to do as he was told. Kyle smelled musky and masculine, and the closer he got to his balls, the more the smell of him enveloped James. He tentatively stretched out his tongue and then drew back, shaking his head. "I can't do it." He sniffled, looking up at the bigger male, his voice small. "Please don't make me."

Kyle backhanded the boy viciously. "You want me to hurt you, is that it? You want me to beat the shit out of you? I don't want to do that, but I will, if you make me. You either take my cock, or I beat you unconscious. It's your fucking choice. You be my bitch willingly or I make it hell for you. My patience is running out, whore. Suck my balls."

Sobbing quietly, James leaned in again. This time, he didn't hesitate, dragging his tongue over Kyle's balls before he took one in his sweet, hot mouth. He sucked on one, then the other, giving Kyle's balls a nice tongue bath.

"Oh, yeah, that's it, bitch. You're getting the idea," Kyle said, jerking himself off lazily, pre-cum dripping into James' hair. Kyle just enjoyed the sensation of having a reluctant pretty boy suck his balls before deciding that he'd have enough. He wanted to ram his cock somewhere warm.

"Normally, I'd draw this lesson out, showing you how to suck cock properly, but you've been such a fucking tease that you'll have to wait next time for a real lesson," Kyle said, fisting a hand in James' hair. He tugged the boy's head back, rubbing the head of his cock over those pretty lips. "Now open up and suck. Don't bite, no matter what, or I'll rip out every single one of your fucking teeth. Shouldn't be too hard to get hold of pliers."

James whimpered and did as he was told, opening his mouth hesitantly, his hands gripping Kyle's hips like he could stop the bigger man raping him if he tried hard enough. James was nothing compared to Kyle - he couldn't stop anything.

"There's a good bitch," Kyle said, aiming his dick slowly into that warm mouth. "Yeah, that's it, there you go, suck it." His voice was low and throaty. He took his time, sinking into that hot, wet cavern at a nice, slow pace. He felt James retch when he hit the back of the boy's throat and he just laughed, pushing past his new bitch's gag reflex, sinking into the tightness of his throat. He was so big that James' throat bulged visibly. The boy couldn't stop gagging and choking, and it felt so good to feel those contractions around his throbbing dick.

James had never sucked cock before. He'd never even licked one, never mind take one down his throat. The closest he had ever come to anything like that was tasting his own come one time. He gagged and retched around the bigger man's cock, panicking. He couldn't breathe. He tried to snort in air through his nose, pushing at Kyle's muscular thighs. Despite his fear, he didn't dare bite - he was more afraid of what Kyle would do to him than he was of not being able to breathe. For the moment.

"Mmm, yeah, you got a real tight throat," Kyle said, feeling it contract around him as James choked. "Feels as nice as a good, tight pussy. Though I bet your ass will feel better." He pulled back, leaving the fat head in James' mouth, letting the other man suck in a breath of air before he forced himself down again.

Kyle started to fuck James' mouth in quick, brutal slides, raping his throat mercilessly. His cock throbbed at the wet heat of it. He was so fucking boned from feeling and watching the pretty college boy gag around his huge cock. He barely let James take a breath.

"Ow, you little fuck," Kyle said, pulling back. "Watch your teeth." It was nothing, just a little scrape where the boy hadn't been concentrating enough, but it wasn't fucking acceptable when you were sucking someone off. Pulling his cock out of James' mouth, Kyle spat in the boy's face and backhanded him sharply, hard enough to split his lip and send his glasses flying.

James' head whipped to the side. He flicked his tongue out, tasting blood. Reluctantly, he looked up at the other man, his eyelashes wet with tears. "I'm sorry."

Looking down, Kyle smirked. He pressed his foot into James' groin. "What's this, faggot?" he asked. "Sucking off guys gets you hard, huh? Well that's good, I guess. You're going to be doing a lot of that, so it's good that you get off on it like a real fag. Probably means you'll get off on a nice ass fucking, too. You're really gonna like it in here."

"I'm not," James croaked. "I don't." He wasn't a fag, he didn't get off on it. But he couldn't deny that he was hard, his cock throbbing, tenting his white briefs. This was exactly what he barely let himself think about at night. But hushed, late night fantasy with a shameful hand moving under his bed clothes was nothing like the reality. His throat hurt. He'd been humiliated, treated like he wasn't a man, wasn't even human.

This man was going to rape him. And he wasn't going to be gentle about it.

"Well, straight men don't get off on sucking cock, do they, boy?" Kyle asked, pulling James in by his hair. "Fuck, doesn't matter to me either way. I'll fuck you whether you get hard for it or not, all I care about is getting off. Don't much care either way if you get off with me. But you should be thankful. Fags just like you have paid money to suck me off. You're a lucky kid, bitch." Grinning, Kyle rubbed the sensitive head of his dick against James' lips and moaned.

"Now come on, suck it properly." He twisted his hand in James' hair. "Open your mouth, take it inside and suck it. If you do a good enough job, maybe I'll bust my nut in your mouth and we'll save your ass for later. If you can't get me to come, well - then we'll just have to see how well your virgin asshole takes a big dick like mine." Kyle grinned down at the boy. "Come on, you know the alternative is worse. Unless you want me to fuck your ass, I mean."

James paused, breathing hard. He knew that he didn't really have any choice - if he pissed Kyle off, he would pay for it. Slowly, reluctantly, he opened his mouth, letting the bigger man feed his cock to him. James sucked, hollowing his cheeks around Kyle's throbbing dick. He could feel the veins against his tongue, and he tried hard not to let his teeth graze the sensitive skin. His own cock throbbed between his legs. His hands twitched toward his cock before he stopped them, curling them into fists.

Kyle groaned, then laughed. "You wanna touch yourself, fag?" he asked. "You don't get to come until I do. You even try to touch your cock and I'll beat your nuts until they're the size of apples. Fucking faggots. No control." He pulled out again, looking down at his dick. He was so fucking hard, and he was getting bored of that pretty mouth. Kyle was a greedy guy - he wanted to open all his presents at once.

"I guess you want my dick up your ass. Get naked and lean over the bottom bunk. I want your ass in the air."

"No, please," James sobbed, his voice raw and rough from the throat fucking. "I'll suck it. I'll make it feel so good. Please. Please don't make me, I've never done anything like this, please."

"You've got ten seconds before I take your disobedience out on your balls."


	2. First Fuck

**Summary for the Chapter:**

> Kyle finally fucks his new prison bitch's virgin asshole, leaving James unwillingly hard and horny.

James was in quite the predicament -- he was kneeling at the feet of his burly, masculine cellmate, his lips swollen and slick from sucking Kyle's cock, tears streaming down his face, his cute blue eyes wide with horror. Kyle's monster dick bobbed and jerked in front of his face, wet with spit and pre-cum. James couldn't imagine that cock fitting in his ass -- it was the thickest dick he had ever seen, even in porn. But if he didn't bend over and offer his ass up willingly, Kyle would just make him. He was his cellmate's new bitch -- if he didn't play nice, Kyle would just hurt him, would fuck him all the more brutally for resisting and take his frustration out on James' vulnerable, sensitive balls.

When Kyle let out a low, warning growl, James immediately sprang into action -- he didn't want to get his balls beaten. Surely that would be worse than taking that monster dick up his ass?

"Please," he sobbed, even as he stood up to do as he was told. "Please, I can't, I've never taken a dick. You're too big, you'll rip me apart, please." His lip was still bleeding from where Kyle had hit him. Everything more than a few feet in front of him was blurry without his glasses. He was a tiny little weed compared to the huge, muscular man in front of him.

"If I have to tell you again, boy, you know what'll happen," Kyle said, narrowing his eyes at the pathetic boy in front of him. He reached down, stroking his thick, meaty cock a few times. The head was sloppy with pre-cum and spit, his cock throbbing in time to his pulse. All he wanted was to bury his dick in Kyle's tight ass and blow his load.

James hesitated for a second longer before wilting like a flower out of the sun. He peeled his underwear down with trembling hands, his cock still sticking up proudly. It was nothing compared to Kyle's -- a mere five inches, and not all that thick. Kyle's cock was easily twice the size of his, possibly even thicker. Stepping out of his underwear and standing there, a skinny teenage boy, barely nineteen, he knew that his life was over. There was nothing he could do to stand up to this man. If Kyle told him to bend over, James would have to bend over, or risk something worse.

Crying like a baby, far too aware of the laughter and jeering from those that could see him in the cells opposite, he leaned over the bottom bunk, trapping his cock between his stomach and the grimy mattress.

"That's it, there's a good bitch," Kyle husked out, eyeing James' pale, round ass and his straining thighs. "Stick your ass out like you're all in heat for my dick." He stepped closer, smearing the head of his dick over James' buttocks. "You got a real pretty ass, bitch. I'm gonna enjoy stretching it out until it swallows my dick like it's made for it."

Shaking, James helplessly did as he was told. Fisting his fingers into the filthy sheets, he stuck his ass out as far as he could. He trembled when he felt Kyle's hot, thick dick smearing over his skin. James closed his eyes and took in a deep breath, just waiting for it. He knew it would hurt -- it would probably hurt worse than anything that he had ever felt, but maybe if he just got it over with, Kyle would leave him alone.

"Oh yeah, you're gonna be a real good, obedient bitch, I can tell. Maybe I should fuck faggots more often," Kyle said, sliding his huge, warm palms up James' inner thighs. In one powerful motion, he wrenched the boy's legs apart, forcing them wide so that James was completely exposed to him. Kyle looked down at his pretty pink pucker and grinned -- he really was going to enjoy turning that tight little asshole into a cunt. Leaning down, he spat slickly on the hole, laughing as he felt James jump. "Relax, cunt," Kyle said. "You'll like this. Most faggots do."

Kyle wasted little time with teasing James -- he just pressed one thick finger against the boy's tight, twitching hole before forcing it inside, twisting it back and forth, screwing it into James' ass. As much as Kyle wanted to fuck the boy, he knew that fucking a virgin open on his huge cock without stretching him out a little on his fingers first would hurt him, too. He didn't care much if he hurt James, but Kyle wasn't much of a masochist -- when he slid into James' virgin asshole, he wanted it to be tight and slick, not chafing him with the vice-like friction. 

James gasped as he felt Kyle's finger penetrate him -- even the man's fingers were thick. James had played around a few times by sticking a finger up his ass, but Kyle's fingers were twice the size of James', and his hole burned and ached as it stretched. Sobbing into the sheets, James trembled in place as his cellmate violated him, stretching his hole open until it ached and burned.

The boy's hole was deliciously tight. Kyle's dick twitched just at the thought of getting inside that tight, hot hole. He didn't really give a shit about James' comfort, or how much he hurt the boy. As far as Kyle was concerned, James was just a hole to fuck. If anything, he kind of liked it when he hurt his bitches -- it made them clench around his cock so nicely. Twisting his finger inside the boy, he quickly added a second, ignoring James' muffled gasps and whimpers as the stretch hurt him. Kyle fucked him brutally on his fingers for a couple of minutes, opening him up, scissoring his fingers mercilessly as James twitched and cried out in pain under him.

Pulling his fingers out with an obscene, slick sound, Kyle parted James' buttocks and looked at the other's pink hole. It was already starting to look like a cunt -- where it had been tiny and tight before he had shoved his fingers into the boy, it was now slick and open. He watched as James clenched, returning his hole back to that tight, pink little pucker. By the time Kyle was done with him, that pretty pink hole would be gaping open and leaking come like a well-bred pussy.

"I'm gonna fuck you now, James," Kyle husked out, spitting onto his opened hole to make the first slide nice and slick. "I'm gonna shove my big dick all the way into your virgin hole. I'm gonna rape your ass." Kyle grinned, stroking his throbbing cock. "Don't worry, you'll learn to love the feel of my huge dick opening you up. By the end of the month, you'll be begging for my dick. You'll be able to take my fist up your pretty pink asshole. Of course, it won't be so pretty and tiny then, but I'm sure you'll learn how much pleasure your ass can bring. Especially to other people." Kyle laughed and slapped James' ass.

"Now, I want you to reach behind you and open up your cheeks for me. I want you to give me your asshole like a good bitch. I want you to thrust your cunt back at me and open yourself up like the faggot you are. Because really, deep down, you want my dick. You crave it. You want it so bad you can fuckin' taste it," Kyle said, gripping his own dick at the base, aiming it at James' virgin hole.

"I'm not," James sobbed. "I'm not a fag, please, I can't. I'm not, I don't want it, please. Oh God, please don't make me. I'll suck your dick, I'll do whatever you want, just please don't fuck me, it'll hurt so bad, please." He couldn't do it. He just couldn't do it -- it was one thing to lie there and take Kyle raping him. It was another thing entirely to open himself up, press back and offer his virgin hole up to the big man. He clenched his opened asshole, sobbing uncontrollably. If he did this, if he let Kyle fuck him, that would be it. He would be the prison bitch. God only knew how many men would fuck him over the next few years. It all started here.

If he wanted to, Kyle could push in anyway and fuck James right there, whether the other opened himself up or not. But Kyle liked it best when they helped with their own violation -- he liked it best when they opened themselves up for their huge dick, sobbing and crying as they pried their buttocks open while he raped them. He slid a hand between James' open legs and fisted the boy's balls, giving them a nasty squeeze. "Reach behind you and open yourself up for my dick," Kyle threatened.

Nauseating pain shot through James' stomach. His legs jerked. He sucked in a breath and whimpered, tensing up, his balls trying to tighten and draw up into his body to escape the abuse. He arched his back, his hands flying back to his ass. Lying flat over the bed, he dug his fingers into the crack and pried his buttocks open as wide as he could, exposing his slick, pink hole humiliatingly. Anything to get away from the sharp ache of having his balls squeezed. "Please," he whimpered, wincing with pain. "I did it, please, fuck, it hurts."

"There," Kyle said, giving James balls one last warning squeeze. "That wasn't so hard, was it?" he asked, just taking a moment to look at the way his new bitch was spread out for him. He was going to have so much fun with this one. His dick twitched, leaking pre-cum copiously from the tip. Moving forward, he teased the uncut head over James' saliva-slick hole, loving the way the boy whimpered and tensed in anticipation. "You keep your ass opened up and shoved out at me, boy. You gotta show me how grateful your fag ass is for the privilege of my thick cock opening it up. Plenty of guys would love to be in your position, so if you ain't grateful, I'm gonna take my payment out on your nuts."

With that final warning, Kyle grunted and started to force the thick head of his cock into James' virgin asshole. Despite the quick fingering that Kyle had given the boy, it was still hard work to get the head in. Grunting and sweating, Kyle rocked forward, gripping James' hip with one hand and his cock with the other. Finally, with a forceful thrust, something gave. James' tight asshole opened up and swallowed the thick head. Kyle groaned and looked down, laughing as the boy squealed. He could see James' ass stretched obscenely around his cock, the boy quivering against the bed as he held his own ass open for Kyle to rape. "You think that hurts?" Kyle asked. "You haven't felt nothin', yet." He gave an almighty thrust, forcing all ten inches of his thick dick into the kid's ass, encasing himself completely inside the boy's tight, virgin hole.

James whimpered. It felt like someone had shoved a hot poker the size of a baseball up his ass. His insides burned and ached, that thick cock stretching him out in ways that he had never thought possible. He sobbed into the sheets, not daring to let go of his ass, keeping himself spread open for the huge dick violating him. "Please," he whimpered. "Oh fuck, it hurts, I can't take it, please take it out, please. I'll do anything."

Kyle just laughed. "You don't get it, do ya?" he asked, fisting a hand in James' hair, keeping him pinned against the bed, forcing his head down and dominating him completely. He started to rock his hips, grunting as James' tight ass practically sucked at his cock as he withdrew. He looked down, admiring the way the boy's hole bulged out slightly as he pulled his cock all the way back to the head before slamming inside him again, making him take all ten inches with every solid, brutal thrust. "You'll do anything I want anyway. I can make you do whatever I want. No one's gonna to stop me. The guards put you in here with me because they want you to get fucked like a bitch. Dunno why they want it, but they only put guys in with me when they want their little assholes stretched out. Fuck, they'll prolly fuck you themselves the first time they get a chance. You're the new prison bitch. You're gonna take everything that's given to you. You're gonna be fucked an' fisted an' tortured. You're gonna have your nuts beaten and your cock whipped. You're gonna have your ass stretched out beyond your wildest dreams, and you'll love it. So don't tell me you'll do anything, because I can make you do whatever the fuck I want." He fucked the boy brutally as he spoke -- each slide became easier and slicker as James' ass opened up for his thick cock, stretching to accommodate him.

The horror of his situation truly dawned on James for the first time. If what his cellmate said was true, it was worse than just being Kyle's bitch. He couldn't help whimpering as the other man pulled back -- it felt like Kyle was dragging his insides out along with that huge cock. But Kyle was right -- no one came. The only response was jeering laughter and hooting from the other prisoners. Everyone knew exactly what was happening, and they weren't helping him. Instead, they were waiting, thinking about what it would be like to take their turn with the new prison bitch, thinking about all the things they could do to him. James sobbed brokenly, breathing frantically as Kyle fucked him hard, using him for his pleasure. His body was no longer his own -- it belonged to the men in the prison, the guards and the inmates that would use him as a fuck toy for the length of his sentence. They would play with him, stripping him of his masculinity and his humanity until he was nothing more than a hole to fuck. Even as he despaired for his future, James had no idea what the extent of the abuse would be like. He was destined to live for most of the rest of his life as a bitch to abuse, fuck and torture, and it was all sanctioned by the guards who would no doubt want in on the action.

The worst part was, trapped between his stomach and the mattress, James' cock was still rock hard and leaking. Every thrust that Kyle made brushed up against a spot inside James that made him pant and clench, traitorous pleasure shuddering through his body, making his cock throb and his nipples tighten. The fucking was hell, even as his ass opened and it got easier. It stung, burning and aching, every thrust feeling like it was ripping him apart. But in every tidal wave of pain there was a lick of pleasure teasing at his senses, stimulating his helpless body until he panted with a desperate mixture of lust and agony.

Slowly, James started to move with the thrusts. He pulled his ass open further, each thrust taking his breath away. James surreptitiously rocked down into the sheets, grinding his aching cock down into the bed. He moaned throatily, his eyes rolling up at a particularly deep, hard thrust that hit his prostate hard enough to make his toes curl. He clenched down around the thick cock invading his ass like he was trying to keep it inside him -- he truly was a slave to his body. He didn't even have control over his own senses.

Kyle moaned as James' ass milked him like a hot, tight pussy. Grunting, he sped up his thrusts, panting erratically as his balls drew up. James' ass felt so good, tightening up around his huge cock in pulsing waves every time he drove into the boy. Kyle didn't really care for James' pleasure, but even he had to admit that it had a nice effect on his dick.

"Oh, fuck," Kyle groaned, his thrusts becoming jerky, his muscles tightening. "Gonna come in your tight little cunt, fuck." With one last, brutal shove, he pushed his dick as far inside James as he could, shuddering and gasping as he came up his new bitch's ass. Grunting and groaning, he rocked his hips slightly, milking his orgasm for all it was worth. Letting out a low sigh, Kyle pulled back, pulling his cock out of the boy's twitching hole. The once tiny little pucker was now slick and open, gaping slightly after the hard fucking that James had been forced to take. "You should see how stretched out your asshole is," Kyle said, sliding his thumbs inside of James, pulling him apart, watching as come leaked out of his hole.

James just whimpered into the sheets at the humiliation of having his well-fucked, aching ass opened up and exposed. He could feel the other man's come leaking out of him. His dick twitched and throbbed underneath him and he couldn't help but rock his hips slightly, unbearably aroused with no relief in sight. "Please," he groaned out -- this time, he wasn't begging for mercy, but something else entirely. His hands flexed, keeping his buttocks pulled open -- he didn't dare let go before he was told. With just an hour in the cell with Kyle, he was already well and truly broken, submissive to the other man in every way.

"Mmm, your hole's really coming along nice. It's already looking like a nice, slick cunt," Kyle said, slapping the boy's thigh and pulling back. He chuckled as James begged him -- the way the other flexed his hips against the bed made it clear exactly what he wanted. "Maybe you won't find it so bad here, faggot. Since you seem to enjoy cock so much. Don't worry, you'll have access to all the cock you can handle and more. But if you so much as touch your dick, I won't be happy. Your cock and balls belong to me now, and you don't get to come unless I say you can. How else are you going to learn to come just from having your ass stuffed? By the way, the bottom bunk's yours, so I hope you haven't made too much of a mess." Kyle grinned and tucked his cock away, looking down at the pathetic, broken college boy.

"Why don't you go over there and show the guys opposite us your well-fucked pussy? Press your ass right up against the bars and spread your cheeks so they can get a real good look at your hole. It'll give them something to look forward to later."


	3. Guards, Guards!

**Summary for the Chapter:**

> James learns that the prison guards aren't going to help him - if anything, they're keen to get in on the fun.

James lay on the bunk, sobbing. He had just had his ass raped by a huge, thick cock. What was worse was that Kyle had made him hold his own ass open for it - even more pathetic was the fact that James still didn't quite dare to let go. Another man might have put up more of a fight, but deep inside, James was submissive. Whereas another man would have needed much more force to bend to Kyle's will, a part of James that he didn't even know existed craved being dominated by a bigger, masculine, more powerful man like Kyle. There was no clearer evidence than the hard, thobbing cock between James' legs, trapped between his stomach and the mattress, leaking sloppy pre-cum all over the bed that he would be sleeping in later. His ass had been opened up from a tight, pink little pucker into an open, slick hole. He clenched, trying to close it, but it returned back to its open state.

Of course, his hole would heal and tighten again, given a little while. It would return to a nice, tight little pucker, perfect for ruining again, and again, and again. James would be fucked in so many ways that by the time he finished his sentence, he wouldn't be anything but a fucked-out cock slut that craved cock and domination. But at the moment, James was very much at the beginning of his journey, and he was still trying to come to terms with his new role as the prison bitch, though is throbbing cock certainly seemed to like his change in circumstances.

"Go on, then," Kyle said. "Go and show off your pussy. I don't like having to repeat myself."

Again, another man might have put up more of a fight, but James' balls still ached from his earlier punishment (for not compying fast enough). He let go of his ass and got up off the bed. His knees were shaky from the brutal fucking he had received, and his dick, which was of average size (though dwarfed in comparison to Kyle's massive cock), was obviously hard and throbbing, wet at the tip.

Crossing the cell, James reluctantly put his back to the prison cell, much to the pleasure of those that could see into the cell. There was whooping and jeering as he leaned over and reached behind him to spread his hole, showing off his opened, fucked-out hole, still leaking come and a little bit of blood where Kyle's dick had been too much for him. His cock throbbed between his legs, a reminder that some sick part of him was getting off on all this.

"You look so pretty, like that. Look at you, your faggot cock all hard for me," Kyle said, leaning against the wall and just watching James for a moment, surprised but pleased by how obedient the slut was being. That time, he hadn't even needed to tell James to bend and spread twice. "Just stay there and let everyone admire your well-fucked ass for a little while."

James stood there for almost half an hour, tears rolling down as his cheeks. He didn't dare move from his position, despite the fact that his muscles protested at the position. The whole time, he showed everyone that could see his spread, opened hole. He could hear the laughing and jeering, could hear promises about how they were going to wreck his hole later, jokes about bending over in the shower. It made his cheeks heat with humiliation, though his cock never quite went down.

Then, the sound of doors opening caught his attention. The guards were making their inspection.

"Please," James said, turning as the guard approached. "Please help. H-he raped me, I need to-"

"Did I say you could turn around, bitch?" Kyle said, looking up lazily from the book he was reading, apparently completely unconcerned by the arrival of the guard.

"That's a very serious accustion, inmate," the guard said. He was a burly man, not quite as large as Kyle, but certainly bigger than James. There was a cruel edge to his smile, something hard in his eyes. James' stomach sank. "You'll need to provide evidence before I can take any action, I'm afraid. I can see you're already naked - why don't you turn around and show me what he allegedly did to you?"

James already knew it was a trap. He was not a stupid boy - he had been in college, after all. Foolish yes, and perhaps a little naive, but he already knew this guard wasn't going to help him. He also knew that the guard had absolute power over him, more so than even Kyle did. He forced down a sob and turned around. This time, he didn't part his cheeks so willingly - he wasn't that much of a bitch, not so quickly.

"I'm going to need to see better than that," the guard said. "Bend over, and part your ass cheeks for me." He paused, then grinned. "Just like you were doing before."

With a sinking feeling and a wrecked sobbing sound, James bent forward and parted his ass cheeks.

"Well," the guard said. "It is looking a little like a pussy, but you could have arrived like that." A ridiculous accusation, since his ass was still a little slick from the brutal fucking he had received. "I better check, to be sure."

James already knew what that meant. He tensed, expecting a probing from fingers. He did not expect what came next. Something big and cold pressed against his hole, not quite as big as Kyle's monster cock, but bigger than a normal dick. With little preamble, the object was forced into his still-tight ring, making James jump and gasp. It went in much easier than it would have done a mere hour before, but it still wasn't an easy fit, his ass burning and aching at the penetration.

The guard had just inserted his baton deep into James' asshole. Kyle watched curiously, reaching down to squeeze his cock slowly through his jumpsuit. That was a hot sight, James bent over and presenting his pretty pussy to the guard whilst the guard worked the baton in and out of James' guts.

The guard fucked James on the baton, admiring the way his cunt practically slurped and sucked at the object.

James, for his part, jerked every time the baton bottomed out in him. It didn't hurt as badly as Kyle's cock, but it certainly wasn't a pleasant feeling. Except that almot every time the guard thrust the baton inside of him, it hit a secret, hidden place, a place that made his cock twitch and leak. After five minutes of being fucked like that, James was panting and flushed, his dick standing at full attention again, throbbing and begging to be touched. He squirmed in place, not daring to let go of his buttocks but desperately wanting to stroke himself. He was blushing with humiliation at his responses - he wasn't a faggot, he didn't want this, but he couldn't deny the way his cock pulsed with his heartbeat.

The guard pulled the baton from James with a slick, obscene sound. "Well," he said, apparently coming to his conclusion. "Your ass loves being fucked way too much for it to be rape. Rape is a very serious accusation, you know. I'll have to let the other guards know that you're one to cry wolf." With that, whistling, the guard went on his way, completely uncaring (or perphaps even enjoying) poor James' predicament.

James stayed where he was, ass still parted, his hole once again slick and opened up from being fucked - once by a cock, and now once by a thick guard's baton. His cock bobbed between his legs as he trembled in place, the reality of the situation once again hitting him. Everything that Kyle had said was true - the guards didn't care. Worse, the guards would be contributing to his abuse. He really was going to be the prison bitch, for every single man that wanted him. And he was pretty enough that nearly everyone would want him.

Kyle was eyeing James contemplatively - watching James get fucked by the guard's baton had gotten him hard again. He rubbed at his cock, contemplating what he wanted to do to the pretty bitch next.

"You really are a faggot cock slut, aren't you, bitch," Kyle said. "Say it. Tell me that you're a faggot cock slut who loves having your ass fucked."

"I-I don't," James said, looking at Kyle, his eyes wet with tears. "I'm not."

"Are you going to make me ask again?" Kyle asked, his voice low and threatening.

James chewed at his lower lip, not saying anything until Kyle started to get up. "I- fuck. I'm a cock slut," he said, his voice quiet.

Kyle smiled, and settled back into his chair. "That's a good start," he said. "But that's not what I said."

James closed his eyes and took a breath. Tears rolled down his cheeks. "I'm a faggot cock slut and I love having my ass fucked," he said, quietly, resigned.

"Better," Kyle said, thoroughly amused. James was so easy to bend to his will, so easy to break. He was going to have a lot of fun making this one do the most depraved things, trying to see where his limits were. Kyle was starting to get the idea that James didn't have any limits, given the right... motivation to do what was asked of him.

A buzzer went, saving James' ass from another raping. Unfortunately, James had no idea about what else he was in for.

"Shower time, bitch," Kyle said. "Since you're such a faggot, cock-loving slut, if anyone tries to talk to you, that's exactly what you're going to tell them. If anyone speaks a word to you, you tell them that you're a faggot slut who loves having your ass fucked, you hear?"

James' heart sunk again. His stomach twisted. It was bad enough having Kyle and the guard abuse him, but he knew that if he did what Kyle asked, the whole prison would soon know that he was nothing but a fucktoy for them to play with. Miserable, he cast his eyes down toward the floor.

"What are you going to tell them, slut?" Kyle asked, patiently.

"That I'm a faggot cock slut and I love having my ass fucked," James repeated, dutifully.

"Good boy," Kyle said. "And don't think I won't find out if you don't. If you disobey me, your balls are going to pay the price."

The prisoners were being sent for their showers in blocks. Kyle would be accompanying James - he had plans for the boy. After all, he liked his bitches to be nice and clean.


	4. Hose Down

**Summary for the Chapter:**

> James is taken to the showers and forced to tell everyone that he is the new prison slut. After that, he is subjected to an agonising enema, filling him until he cries for mercy.

**Notes for the Chapter:**

> Please note: this story contains graphic descriptions of non-consensual sex. This chapter contains humiliation, BDSM, CBT (mild) and an enema/slight inflation fetish. If the latter is not your cup of tea, please skip this chapter. Please note that the author does not condone any of this in real life.

When it was their turn, Kyle contemplated making James go down to the showers naked – that would certainly send a message. But there was no fun in rushing things. Kyle had a lot of time to ensure James’ utter debasement – one day soon, James wouldn’t be allowed to go anywhere without crawling, naked, offering himself up to any man who wanted him. Kyle was patient to allow him to wear clothes. This time.

James, completely oblivious to how close he had been to making the trip down to the shower naked, dressed. They stepped out of the cell together, Kyles’ hand a commanding presence on the back of the boy’s neck, guiding him. James’ eyes were still red-rimmed with tears, and his ass still throbbed from the earlier abuse.

They joined the throng of men heading down to the shower.

“Well, whose this?” asked a thirty-something, bald man with a crooked nose. He grinned nastily at James.

James, naively, hoped that Kyle would respond for him. He didn’t get that luxury. Kyle squeezed the back of his neck hard.

“I’m… I’m a faggot cock slut and I love h-having my ass f-fucked,” James said, casting his eyes downward, toward the floor.

The man’s grin widened. “I’d help ya out with that but we’d hold everyone up,” he said. “Maybe in a bit, eh?”

“Maybe,” Kyle said. “He needs cleaning up first. Come round during rec and I’ll make sure he spreads for you.”

“Yeah?” the man asked.

“First fuck’s free for friends,” Kyle said. “After that, it’s a pack a go. Half for his mouth.”

“A pack?” the man asked, raising his eyebrows. That was expensive.

“Yeah, have you seen his face? He’s cute as fuck, if you’re into that. Plus he was a virgin before I fucked him. Still nice and tight, though not for long. He cries real nice, too. Show him your face, slut.”

So this was what his life was going to be? Pimped out for cigarettes. James shifted in place, his eyes on the floor. Disobeying wasn’t worth it, for such a simple order, no matter how it was phrased. Flushing, he raised his face toward the man.

“Aye,” the man said. “I’ll try ‘im out, mind. For free, you said.”

“Sure. Might not want to wait for too long, though, if you want a tight hole to fuck. I can tell this one is going to be a favourite.”

James winced. He licked his lips. “Please,” he said.

“What’s that, slut?” Kyle asked, still gripping the back of his neck, marching him forward toward the showers.

“Can’t I… I want to be all yours,” James said, not sounding at all convincing. “Your personal fuck slut.” It was simply a matter of self-preservation. He didn’t know how he could exist, bending over for the entire prison as some form of currency.

Kyle laughed. “It’s selfish not to share. You don’t want me to be selfish, do you?”

James’ stomach asked. He opened his mouth to respond, to beg some more, but then they were at the showers, and Kyle shoved him toward the changing room. “Everyone, this is James. James, why don’t you introduce yourself. The way I taught you.”

James paled. There were at least thirty men in the room. “I can’t,” he said, his voice a near whisper.

“You will,” Kyle said. “Or I’ll have you bend over that bench and give your ass to every one of them, right now.”

James swallowed, his hands clenching, his face flushing with humiliation. “I’m a faggot cock slut and I love having my ass fucked,” he said, so quietly that only those nearest him could hear him. They laughed and nudged each other, eyeing him up and down.

“Louder,” Kyle said. “Don’t make me ask it again. They better hear you in the next fucking cell block.”

James took in a breath, slanting his eyes down toward the ground, not wanting to look at them. “I’m a faggot cock slut and I love having my ass fucked!” he exclaimed, to the whole room. The room immediately erupted into laughter and raucous comments.

“Good slut,” Kyle said. “Now get undressed and get into the shower blocks.”

Kyle stepped away, getting undressed smoothly and quickly, leaving James to his own devices.

James lingered, hoping that if he just took long enough, he would somehow be able to avoid whatever was coming next. However, Kyle didn’t wait for him, leaving the room, and James became increasingly aware of the men staring at him. Suddenly, he felt unsafe. More unsafe than he felt with Kyle, somehow. He finished undressing hurriedly, aware of the eyes raking his flesh, swallowing as he hurried after Kyle before he was gang raped in the changing room. A fate which he felt sure he would be punished for.

Kyle was already under the water, and James had to admit that he was magnificent. He stopped, staring for a moment, watching the water sluice over smooth, muscular skin. Normally, he would never stare like that, but Kyle had fucked him. Kyle had dominated him thoroughly. When Kyle turned, James got a magnificent view of that thick cock, and he wondered how something like that had ever fit inside him. Kyle chuckled.

“And you say you’re not a faggot,” he said.

James flushed, deeply. The comment immediately sent his gaze back to the floor. Other men showering eyed him with a predatory gaze. James stepped toward Kyle without even having to be told.

Kyle shoved James under the spray of water with some soap. “Get clean. Quickly,” he said. The water was lukewarm, but James did as he was told, scrubbing quickly. He didn’t want to be punished over something so simple.

When Kyle decided that James was clean enough, he shoved the boy out of the way. “Kneel,” he said. “Wait on your knees until I’m done.”

James looked down at the scummy floor, his face twisting. He looked at Kyle, not quite believing the order, and was met with a hard backhand for not obeying immediately. His head snapped to the side. Immediately, he fell to his knees, trying to avoid more. He licked his lips, surprised when there was no blood. The blow had stung.

Kyle washed himself. Men filtered in and out of the shower, leering at James, kneeling next to Kyle’s feet. Kyle reached for the shower head. He unscrewed the head slowly, and the hose came free, still spraying water. James watched, confused – was he allowed to do that? What was he doing it for?

“Get on your hands and knees,” Kyle said, moving behind James, the hose in hand.

James looked behind him, still confused, but he did as he was told. Then, he felt something at his hole, and he realised what was happening as Kyle slid the hose inside him.

“No!” James yelped, reaching behind him to dislodge the hose. He could already feel the water gushing into him, a little too warm to be comfortable.

“You little shit,” Kyle said, as James tried to pull the hose free. He reached a hand between James’ legs and squeezed his balls hard.

James screamed, immediately slapping his hand back onto the gross tiled floor, retching. The pain was so sudden and so intense that he couldn’t cope with it, black hovering at the edges of his vision. As soon as he stopped trying to resist, Kyle stopped squeezing his balls, but the pain lingered.

“You’ll stay right where you are until I come and get you,” Kyle said, just watching for a moment.

James whimpered. The water was gushing into him at an alarming rate. He was already starting to feel a little uncomfortable. Worse, Kyle left the room, presumably to get dressed. After a minute or so, James really started to sweat. He felt bloated and uncomfortable. A cramp ripped through him, making him gasp, his toes curling. His nails clawed against the tiles as the water kept filling him, his toes curling as he tried to endure it. He fixed his eyes on the door of the shower, frantically praying that Kyle would return as the pressure got worse and worse.

His stomach rounded slightly, like he had just eaten a five course dinner, and Kyle still didn’t return. James was in a world of pain, his teeth clenching. At some point, the pain just didn’t seem worth it, and before he’d reached a conscious decision, he reached behind himself and pulled the hose out. He emptied himself, crying at the humiliating splash of water leaving his bowels. He cried because he couldn’t believe that he had fallen so far already. He cried because he knew he would be punished, probably worse than he could imagine. He cried because the cramps were the worst pain he had ever experienced. He cried because he was never going to be the same.

Kyle came back to James sobbing, still on his hands and knees, still emptying himself. He sighed, walked up, and put his hand on James head, like he was a dog.

“Are you sorry?” he asked.

James blinked, not daring to look at Kyle, quaking in place. He was already do afraid of the other man. “Y-yes,” he said. “I’m sorry. I didn’t mean it. It hurt so much, and you didn’t come back, please. I was trying so hard to be good.”

“Were you?” Kyle asked. “I got caught up, but that’s no excuse.” He paused, running his fingers through James’ wet hair. “Do you want to make it up to me, or do you want me to punish you? It’s up to you.”

There was no question. “P-please let me make it up to you, please,” he said.

Kyle nodded. “I thought so,” he said. Moving behind James, he reached for the hose, and slipped it back into James’ body.

James sobbed, tensing. He didn’t think he could do that again. He also knew that he had absolutely no choice. The water gushed into his body. James whimpered as the cramps started again. He already felt tender and bloated from the last round.

Luckily for James, just as the pressure was once again becoming unbearable, the water was turned off, the showers emptying out. Kyle didn’t remove the hose, though, leaving James to sweat, sob and cramp, his stomach visibly bloated.

Kyle was just about to pull the hose out when two guards entered the shower block – one of them was the same guard as before, the one who had shoved his baton inside of James. He took one look at the scene, laughed, and nudged his friend. “This is the little faggot I was telling you about.”

James was in too much pain to do anything but moan.

“Inmate, leave him here, we’ll take care of him. Get back to your cell. Shower’s over.”

Kyle paused, reluctant. He sent the guards a surly expression – he knew that he didn’t have any choice, but he had plans for the boy. Plans that were being interrupted by the guards.

“Get the fuck outta here,” the other guard said. Kyle reluctantly did as he was told, exiting the shower room, leaving James to his fate. Wasn’t worth putting himself at risk.

One of the guards moved forward and pulled the hose out of James.

In too much pain to even feel embarrassed, James just moaned with relief, emptying himself out onto the floor, his stomach grumbling loudly. The water, for the most part, ran clear. He was nice and cleaned out. Trembling, exhausted, he kept his eyes on the floor.

“Get him,” the other – new – guard said. “I’m not fucking playing with him here, let’s take him to the rec room.”

Which was how James ended up being escorted – naked – by two guards to the guard’s break room so they could play with him at their leisure.


End file.
